4-Methylmorpholine → (Z)-tert-butyl 3-(4-(2-methoxyethyl)phenoxy)acrylate

HRID 1025365

Reaktionsgleichung

Reaktionsgleichung von HRID 1025365
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[C:12]([O:16][C:17](=[O:20])[C:18]#[CH:19])([CH3:15])([CH3:14])[CH3:13].CN1CCOCC1>C(Cl)Cl>[CH3:1][O:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11]/[CH:19]=[CH:18]\[C:17]([O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:20])=[CH:7][CH:6]=1

Komponenten

5

Edukt 3

HCID 79724-MethylmorpholineHCID 925164-(2-Methoxyethyl)phenolHCID 543038tert-Butyl propiolate

Produkt 1

HCID 67168776(Z)-tert-butyl 3-(4-(2-methoxyethyl)phenoxy)acrylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

a mixture of 4-(2-methoxy ethyl) phenol (1.547 g, 10.3 mmol), propiolic acid tert-butyl ester (1.367 g, 10.8 mmol) and N-methyl morpholine (1.18 mL, 10.8 mmol) in CH2Cl2 (15 mL) was stirred at room temperature for 24 hours. The mixture was absorbed on SiO2 (20 g) and purified by column chromatography using a mixture of methylene chloride/hexane. The product was obtained as a two to one mixture of (E)/(Z)-tert-butyl 3-(4-(2-methoxyethyl)phenoxy)acrylate isomers (2.0 g).

Aufarbeitung

  1. customThe mixture was absorbed on SiO2 (20 g)
  2. custompurified by column chromatography
  3. additiona mixture of methylene chloride/hexane

Quellen und Nachweise

ORD-Eintrag
ord-e47ee3856d324f2090501d56303869db
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08729075B2

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